Register Now
Already registered? Login

Sign in to take advantage of all this site has to offer. Save your favorite listings and searches – also receive email updates when listings you like come on the market for free!
*Contact Information is NOT Shared*

Janice White
Century 21 Fine Homes & Estates
Blue Sky Realty Group

720 Celebration Ave., Ste 100

Celebration, FL 34747

Email Janice
Janice's Testimonials

Quick Search

view all



No Min.

No Max.

Homes for Sale in Winter Park, FL

Winter Park is a suburban city in Orange County, Florida, United States. The city was founded as a resort community mainly by northern business leaders in the late 19th and early 20th centuries. In the 1860s, Winter Park became the first planned community in Central Florida, strategically built around the railroad which served commerce and travel.  Winter Park’s main street includes civic buildings, retail, art galleries, a private liberal arts college, museums, a park, a train station, a golf course and country club, a historic cemetery, and a beach and boat launch. Mediterranean, Greek, Victorian, Revival, and Arts and Crafts period architecture create an eclectic atmosphere with many of the structures being more than 100 years old.

Known as the 'City of Gracious Living,' Winter Park, Florida, is one of America's most appealing cities. Its scenic beauty, tranquil environment, and abundance of art and culture have made it a showplace residential area since the late 1800's. The city is home to Rollins College, Full Sail University and the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass. Winter Park features open park space, residential areas, and a street-side shopping district along Park Avenue where visitors can experience Winter Park’s charm with outdoor cafés, bistros and upscale specialty shops and boutiques.  The area is host to frequent art and music festivals. And, although it feels as if it's worlds away, it's only a few miles from downtown Orlando.



The population was 27,852 at the 2010 census. Winter Park is part of the Orlando–Kissimmee Metropolitan Statistical Area. 


Winter Park Neighborhoods

The scenic Olde Winter Park area is accented by small brick-lined streets that meander through quaint neighborhoods graced with old majestic oak and camphor trees forming a canopy draped with Spanish Mosss along the streetscape.  Picturesque lakes with old Venetian canals surround residential areas.  Beautiful parks, old majestic trees, and botanical gardens are abundant. Providing active and passive green space for residents and visitors is a priority for Winter Park city planners and helps maintain the charm that Winter Park has to offer.

Hannibal Square is what is called a legacy community.  Hannibal Square—the “west side”—was officially founded in 1881, only 40 years after Florida became the 27th state, and 14 years after the state reentered the Union.

From its' beginnings, Hannibal Square was rooted in faith, family and community. The west side was characterized by high levels of education, business and home ownership, and professional standing among its' African American residents.

For over one hundred years, the intersection of New England and Pennsylvania Avenues was the heart of the shopping and entertainment district for the local African American community.  Today's Hannibal Square merchants enjoy the neighborhood feeling that comes from being part of an existing community of residences, churches, community centers, playgrounds, train access and beautiful parks.

Although time has changed the character of the neighborhood, the merchants work hard to preserve the village ambiance, and to celebrate and support what is remaining of the historic neighborhood.


Park Grove was established in the late 1950's. The first houses were built in 1960. Park Grove can be identified by its pink subdivision wall, a small park located near the entrance at Park Avenue and Summerland Avenue and the oak-lined streets.

The homeowners association was developed in the mid -1960's when addressing issues fell upon the residents. The Board hosts an annual block party each year. Some of the activities at the block party have included street parties, barbecue dinners, chalk art on the streets, decorated bike competition, parades, children's theater group, Halloween parties and caroling and luminaries at Christmas.

The land on which Northwood Circle is located was formerly owned by Callie Colston Green whose desire was to see a subdivision developed for blacks.  Her desire became a reality when she teamed with the Sulphur Investment Corporation and H & M Construction Company of Winter Park to make it happen.

What makes this community unique and historical are the circumstances that brought about its development at that time.  Northwood Circle was the first and only subdivision in Winter Park that was conceived by blacks and developed for blacks; buying homes and living in other subdivisions in Winter Park at that time were not accessible to blacks. 

Orwin Manor remains one of the more desirable areas to live and has been cited as one of the fastest appreciating neighborhoods in the Orlando area. To insure that the neighborhood maintains its quality of life, a number of Orlando and Winter Park residential ordinances are strictly enforced.   You will find that once again, many young couples are raising their families in Orwin Manor. Its’ convenient location, variety of architecture, historic homes, mature street lined tree canopies make Orwin Manor a wonderful place to live.

The first homes in Orwin Manor’s Westminster Section were built starting in 1925. These homes were Mediterranean themed styles which virtually defined Florida's great 1920’s land boom era along with a variety of styles including colonial revival, mission, and bungalow. The streets of Orwin Manor, were lined with curbs, sidewalks, streetlights with underground wiring, oak trees and palms. When the land boom went bust, construction in Orwin Manor slowed and did not pick up again until the post WWII building boom when many vacant lots were cleared for new homes. Few of these used the Mediterranean themed styles from the previous decades.

Sevilla began its development in 1970. The land now contains 63 lots. Most of the homes were built in the early 1970’s, however, two homes have been built since 1995. The homes were built by prominent builders of the day including Charles Clayton who lived in Sevilla with his family for many years. Many of the original owners still reside in the community.

The community of Sevilla is located just off Pennsylvania Avenue in the heart of Winter Park; minutes away from Rollins College and the Park Avenue Shopping District. The community is bordered by Fawsett Road, Lake Sue and Mead Botanical Gardens. There is one entrance to the community on Pennsylvania Avenue.

Situated along the shores of three sparkling lakes, Windsong is a 200 acre community located in the center of Olde Winter Park and mirrors the old-world charm of the area. Windsong’s neighborhoods were developed around the Windsong estate which was built in 1904 by a Chicago industrialist.



Winter Park is home to the second oldest golf club in Central Florida.  The course makes its way through the downtown Winter Park area with its narrow, tree-lined fairways and postage stamp, bunker guarded greens and provides a challenge for beginning to expert golfers.

Winter Park offers a wide selection of festivals throughout the year to satisfy everyone's interests and the city draws thousands of visitors to its’ annual festivals including the Bach Festival, the nationally ranked Sidewalk Art Festival, and the Winter Park Concours d'Elegance. 

The Winter Park Sidewalk Art Festival is one of the nation's oldest and largest juried outdoor art festivals, rated among the top shows by Sunshine Artist and American Style magazines. In 2012, about 1,200 artists from around the world applied for entry, and an independent panel of judges selected 225 national and international artists to attend the show. The National Endowment for the Arts, the White House, Congress, and many others have honored the Festival for promoting art and art education in Central Florida. An all-volunteer board of directors runs the annual festival, now in its 50th year.

408 Results Days on Site (new to old)
$3,895,000 New For Sale
375 Virginia Drive
Winter Park, FL 32789
5 beds, 4.5 baths | Single Family Home
7,538 sq ft; lot: 1.32 acres
$265,000 New For Sale
7009 Citrus Point Court
Winter Park, FL 32792
3 beds, 2 baths | Single Family Home
1,470 sq ft; lot: 9148 sq ft
$995,000 New For Sale
4 beds, 2.5 baths | Single Family Home
3,501 sq ft; lot: 16553 sq ft
$1,795,000 New For Sale
315 E New England Avenue #27
Winter Park, FL 32789
3 beds, 3.5 baths | Condo
3,125 sq ft; lot: 0.63 acres
$375,000 New For Sale
4264 Steed Terrace
Winter Park, FL 32792
4 beds, 2 baths | Single Family Home
2,275 sq ft; lot: 13068 sq ft
$276,000 New For Sale
4015 Waterview Loop
Winter Park, FL 32792
3 beds, 2.5 baths | Single Family Home
1,567 sq ft; lot: 5663 sq ft
$199,000 New For Sale
1500 Gay Road #10D
Winter Park, FL 32789
2 beds, 2 baths | Condo
1,026 sq ft; lot: 2178 sq ft
$1,165,000 New For Sale
1831 Laurelton Hall Lane
Winter Park, FL 32789
4 beds, 4.5 baths | Single Family Home
4,019 sq ft; lot: 13504 sq ft
$255,000 New For Sale
2310 Atomic Court
Winter Park, FL 32789
3 beds, 1.5 baths | Single Family Home
1,207 sq ft; lot: 8276 sq ft
$325,000 New For Sale
1020 Minnesota Avenue #7
Winter Park, FL 32789
3 beds, 3.5 baths | Condo
2,000 sq ft; lot: 1307 sq ft
$795,000 New For Sale
1276 S Pennsylvania Avenue #12
Winter Park, FL 32789
3 beds, 2.5 baths | Condo
1,957 sq ft; lot: 1742 sq ft
$145,900 New For Sale
2369 Flamingo Way
Winter Park, FL 32792
2 beds, 1 bath | Townhouse
854 sq ft; lot: 3049 sq ft
$475,000 New For Sale
2845 Summerfield Road
Winter Park, FL 32792
4 beds, 2 baths | Single Family Home
2,630 sq ft; lot: 12632 sq ft
$105,900 New For Sale
1695 Lee Road #203
Winter Park, FL 32789
2 beds, 1 bath | Condo
881 sq ft
$300,000 New For Sale
2703 Ambergate Road
Winter Park, FL 32792
4 beds, 3 baths | Single Family Home
1,835 sq ft; lot: 11761 sq ft
$549,000 New For Sale
1712 Arbor Park Drive
Winter Park, FL 32789
4 beds, 2 baths | Single Family Home
1,899 sq ft; lot: 8276 sq ft
$350,000 New For Sale
719 London Road
Winter Park, FL 32792
4 beds, 2 baths | Single Family Home
1,531 sq ft; lot: 9583 sq ft
$280,000 New For Sale
1431 W Brookshire Court
Winter Park, FL 32792
4 beds, 2.5 baths | Single Family Home
1,906 sq ft; lot: 5227 sq ft
$1,295,000 New For Sale
1660 Mizell Avenue
Winter Park, FL 32789
4 beds, 3.5 baths | Single Family Home
3,798 sq ft; lot: 13504 sq ft
$416,982 New For Sale
2087 Laurelwood Way
Winter Park, FL 32792
4 beds, 2 baths | Single Family Home
1,908 sq ft; lot: 5663 sq ft
Listings 1-20 out of 408 Previous 1 2 3 4 5 Next
Janice White, Realtor

720 Celebration Ave, Ste. 100
Celebration, FL 34747
Phone: 407-973-8762


Joe and Janice are outstanding Realtors. They are an amazing, personable team. They are giving of their time, knowledge and talent. They communicated very well with us, having our best interest in mind. We appreciate their help with this transaction and look forward with the second transaction. Great Partners! Glen and Joan Kozak
View All

Connect With Me


Subscribe to my newsletter...

* fields are required
Real Estate Websites by iHOUSEweb iconiHOUSEweb | Admin Menu